


Pretty Woman

by Kileykao



Category: Critical Role (Web Series) RPF
Genre: Dress Up, M/M, Roleplay
Language: English
Status: Completed
Published: 2019-09-22
Updated: 2019-09-22
Packaged: 2020-10-25 17:37:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,312
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20728157
Author URL: https://archiveofourown.org/users/Kileykao/pseuds/Kileykao
Summary: He doesn’t think much about the dumb clothes that Sam wears for his ad reads until he dresses like Britney Spears.There is something about seeing Sam fully dolled up that makes Liam’s mouth go dry. Something that makes a part of him wants to drag Sam off to a dark corner of the studio and take him apart. He pushes the thought aside because they have a game to play, and they are live on the internet. The first half passes agonizingly slow as Liam watched Sam sitting across from him playing with the braided hair of the wig and adjusting the bra every now and again.





	Pretty Woman

**Author's Note:**

> In response to a prompt on the kink meme of Sam Riegel playing Dress Up
> 
> Also on the Kink Meme

Liam doesn’t think much about Sam dressing up for his ad reads for or for live shows. He’s known Sam long enough to know that Sam enjoys wearing dumb and crazy things to get a reaction out of people. He’s seen Sam in enough customs and weird outfits in their close to 20 years of friendship that it takes a lot to get a genuine reaction out of him. 

He doesn’t think much about the dumb clothes that Sam wears for his ad reads until he dresses like Britney Spears. 

There is something about seeing Sam fully dolled up that makes Liam’s mouth go dry. Something that makes a part of him wanted to drag Sam off to a dark corner of the studio and take him apart piece by piece. He pushes the thought aside because they have a game to play, and they are live on the internet. The first half of the game passes agonizingly slow as Liam watched Sam sitting across from him as he played with the braided hair of the wig and adjusted the bra every now and again. 

His mouth stays dry, for the remainder of the first half. One eye always on Sam watching. He doesn’t say anything to his husband, but Sam knows him well enough to know that as soon as Matt calls break Sam is out of his chair and pulling him off in the direction of their shared office. 

The lights are off in there, as expected, but Sam flips the switch as he drags Liam into the room and shoved him down onto the couch. Liam sits there wide-eyed staring openly at Sam now. The skirt comes to just above his knees, swaying as Sam turns and locks the door behind them. The heels that Liam did not know Sam was wearing and was not expecting in any way add another 2 or 3 inches in height to his already tall frame, and click against the floor as he walks. When Sam turns back to him he drops down onto the couch straddling Liam’s legs, Liam can feel himself getting hard with that. A beautiful man sitting on his lap, it’s not hard for him to get hard. His hand hesitates for a moment, before setting on Sam’s waist. 

“You look about ready to eat me, Mr. O’Brien,” his voice slightly pitched higher, more feminine, but not quite as degrading as Nott’s voice, or as annoying as the voice he had used for the ad read a few hours before. Liam’s brain freezes for a second, nothing but static as his jeans get progressively tighter and Sam painted nails come and lightly scrape across his bare cheek. 

“Uhh,” Liam tries desperately to think of something, anything, to say in response. Instead, he’s just met to Sam’s laughter. 

“We don’t have time for you to properly have fun, and I do want to get out of these clothes before we go back on,” the front of Sam’s skirt is just the faintest bit tented now, and without even realizing it his hand moves from the faintest bit of bare skin showing on his wait and palms at the tented fabric. Sam moans, both of them mentally trying to figure out if they would have time to mess around with each other and still have enough time to clean up and be back on camera in time. 

Instead, Sam leans forward, and whispers into Liam’s ear, “Can I borrow you this weekend?” Liam nods, eagerly and pulls Sam down into a kiss, rough and claiming. Liam hands move up and cup around the fabric of the bra, squeezing, and Sam’s eyes light up at the thought. 

They don’t get much further than that, as Sam’s name is being called and Liam’s phone starts ringing with Amy’s name on the screen. 

They both pull away and adjust themselves before heading off in separate directions to recollect themselves for the second half of the game. 

**

A few days later Liam gets a text from Sam telling him that he’s expected to be at his house at 7 o’clock that night, and to dress up for their date. 

He doesn’t know what Sam has planned, but he puts on a suit and red tie, at Sam’s request, before he heads over to Sam’s place anyway. He doesn’t really know what to expect when Sam opens the door, but when he gets from the younger man isn’t at all what he expected. 

What he gets is Sam standing much taller than him. It’s enough extra height that he doesn’t need to look down to know Sam is in heels. What he gets is Sam in a wig, this one much more natural than the Elsa wing he on Thursday. It’s a slight bit lighter than his own hair color, and much longer coming down to rest just past his shoulders, and beach curls bouncing as Sam moves in the slightest. 

What he gets is Sam, with a bright smile on his face saying hello to him. His voice pitched higher, more feminine, the voice that he used the on Thursday when it was just the two of them. Liam doesn’t need to have a conversation with Sam about what’s going to happen tonight to know what Sam has planned. Instead, he just takes in the sight of his hus-- wife, his wife for the evening, whispering a hello back. 

Sam’s face is clean-shaven again, with eyeshadow on his lids and eyeliner framing his eyes. The eyeshadow is softly applied, light pinki-sh red with a slight sparkle in it that it just barely shimmers in the light. His lips are bright red too, and it matches the dress he’s currently wearing. It’s lace and as red as the lipstick on his lips right now. The dress is short for him. Liam can imagine that the dress on someone of a smaller frame it would be knee-length, but on Sam, the fabric just barely reaches to mid-thigh. 

The lace that covers the dress is pretty, with intricate details of roses and leaves spread across the fabric, a red ribbon across the waist. The skirt of the dress poofs out enough that Liam is pretty sure that if Sam were to get a boner, it won’t be that noticeable like it had been in the Britney skirt. (A part of Liam wonders if that was a conscious choice on Sam’s part when he was choosing his dress for tonight). Also, the fabric across Sam’s chest is raised enough for him to know that Sam is wearing some kind of padding underneath. His eyes pan down and he can see that the heels that Sam is wearing are also red and have ribbons, tied into neat little bows, wrapping around his ankle. 

Liam doesn’t know what to say, he’s standing in the doorway of the house, with Sam standing more than a few inches over him -- Liam is pretty sure that in these heels Sam would have an inch or two on Travis too -- mouth slightly agape, taking in the sight. Sam just smiles at him, taking pity on his broken brain, and bending down into a kiss. Sam’s right-hand wraps around his wrist and Liam can see that Sam’s nails are the same shade of red as the dress and his lipstick, pulling in the house. Liam’s mouth is dry again, and he licks his lips as he was being led in the general direction of the kitchen, before saying, “You look gorgeous tonight Sammy, stunning,”

Sam turns back to him, and his left hand comes up and rest on his face, there a ring on his ring finger that is not the normal ring that rests there. From the brief glance that he got of it, he can tell its more flashy, the band thinner than his normal ring, with some kind of gem resting on the top. At that moment with Sam’s hand on his cheek, and ring on his finger that isn’t normally there does it hit Liam that Sam is playing his part to the best of his ability. 

“Only the best for my husband,” His voice is still pitched, and Liam isn’t sure if he can last a threw dinner if Sam keeps talking like that. Everything about Sam tonight strikes a chord within Liam that he didn’t know was there. He doesn’t know what it is about this makes everything that’s happening seem amplified by a thousand. Whether it’s the clothes, or the voice, or just the fact that it’s Sam and went through all this effort just for him, but Liam is looking at Sam and he really doesn’t know how he’s gonna make it through whatever Sam has planned tonight without skipping straight to the end. 

Sam smiles again and leads him into the kitchen. The lights are dim, and there are candles lit on the table. Sam ushers Liam to the table and then brings food out. Dinner is good. Sam is a great cook, and it’s always nice to have a quiet dinner with amazing food and a glass of wine with Sam. 

They hold a steady conversation while eating, talking about life and kids and how they’re recent trips have been, all while Sam maintains the slight high pitched and feminine voice. Sam maintains the voice easily, practiced in the way that voice actors are at maintaining voices for longer periods of time. Liam is pretty sure that he’s never had a dinner with Sam where he’s been semi-hard the entire time since the two of them were in their twenties, and always one step away from jumping each other. 

When dinner is finished Sam took their plates and drops them in the sink. Before returning to the table and dropping himself down in Liam’s lap. He drops sideways, his arms wrapping around the older man’s neck as support. Liam wraps one arm around his waist and lets the other rest on his bare thigh. Sitting with Sam like this isn’t entirely uncomfortable, there’s a slight pressure on his cock that’s been left ignored since he walked in the door, he has his stunning wife in his lap, and like this Liam can that Sam shaved his legs. 

The skin is smooth and free of hair, and Liam feels his mouth water and his cock twitch, a part of him wondering how far up Sam went with the razor for their date tonight. 

Once Sam is relatively sure he’s not gonna tip over onto the floor one of his hands starts to trail down across Liam’s chest before settling next to his thigh pressing down. Liam lets out a moan, and Sam smiles. His lipstick isn’t as bright as it was when Liam got here an hour or so ago, but it’s still much redder than it normally is. 

“Will you take me to bed, Mr. O’Brien,” there aren’t many times where Liam wishes he was built more like Travis, but sitting here with Sam in his lap all dressed for him, asking to be taken to bed, he wishes that he could lift Sam up and carry him off. 

Instead, he pulls Sam to his feet, and pulls him into a proper kiss, “Of course, Mrs. O’Brien,”

(Liam knows he got the name right when Sam’s pupils dilate, the brown being engulfed by the black.)

His arms wrap around his waist, pressing his chest along Sam’s back. It’s more difficult with the few extra inches that the heels add, but Liam guides him through the house in the direction of the bedroom. One hand moving across Sam’s front at first resting just below the waist, pushing down enough to indeed find that the red dress does poof enough that Sam’s hard dick is hidden below it, then moving higher and cupping one of Sam’s breasts. 

He guides Sam to the bed, and he drops down on his back, the dress spread out around him, and the hair of his wig haloed around his head. Sam knees spread and Liam moved in between them. His hands trailing along his thighs. His voice is soft when he whispers to Sam, “Such a pretty woman, all dressed up for me,”

Sam smiled while leaning up, one hand wrapping around his tie and pull Liam down into a kiss. Liam’s hand flutter around Sam one cupping his Breast, or at least whatever padding Sam has under the dress and the other slowly rubbing up against his thigh, his fingers inching higher along bare skin. Sam’s hand are pulling at the buttons of his shirt, his tie quickly being discarded and his shirt not long after.

Eventually, after a bit more teasing, Liam stood shirtless with Sam’s fingers struggling to get to his belt, and Liam’s fingers found underwear. Liam probably should have guessed that Sam took these clothes all the way, but still, when his finger found lace he was surprised. Quickly his hand that was still squeezing and fiddling with Sam’s chest moved down and pushed the skirt of the dress up higher up until it was bunched at his waist. The underwear is lace and just about the same shade of red as the dress with black trimmings and a little black bow just above Sam’s package. 

Liam licks at his lips, and Sam grins. It’s smug and small and mischievous, and after a second Sam says, “The top matches you know,” 

Liam lets out a moan, as his hand returns to Sam’s chest squeezing again, as he whispered: “Like this, or do you want to flip?”

Sam debates for a moment, one of his hands resting on top of Liam’s on his chest, “like this for prep, then I want to ride you, Mr. O’Brien,”

Liam let out another whine, struggling to pull away from Sam, stumbling out of his pants and kicking off his shoe before making it to the nightstand and pulling out a bottle of lube. Liam returned to between Sam’s legs and began to pull at the ribbons of his shoes. 

Each heel dropped to the floor with a thud, and as Liam ran his hands along Sam’s legs before getting back to the bulge, the lace stretched across his cock. He pressed a little, just enough to hear the sound that comes out of Sam’s mouth.

“Do you want to keep your dress on Sammy?”

Sam debated again, moaning as Liam’s finger traced along the pattern in the lace of the underwear, he nodded moaning out, “for now, I do want you to see my pretty bra too, I got all dolled up for you, and I hate to think that you wouldn’t get to see it,”

He pressed down pressing a kiss to Sam’s lips. Sam’s hand wraps around the back of his neck, his red-tipped fingers grabbing onto the hair there, deepening the kiss. 

“My pretty wife, you're spoiling me,”

Sam laughs and Liam’s hands grab at the lace covering him. He pulls the underwear down, his fingers ghosting over his cock as he goes. Sam moans into his mouth, and Liam takes the opportunity to slip a tongue into his mouth. 

They kiss for another moment, as Sam gets his underwear all the way down and kicks it the floor. It Liam’s brain wasn’t mostly mush right now, he probably would have saved the pretty underwear from that fate, but he’s too distracted by Sam, and the wig that somehow still in place, and by how god damn beautiful he is. 

The cap of the bottle of lube snaps open with a click and Liam pours some on his hand. He rubs his palm between Sam’s legs spreading some of the cool liquid, and the younger shives at the cool touch of the lube. “You’re all wet for me,” he pushes the tip of his forefinger into the first knuckle, slowly pushing in and out for a few seconds before continuing, “Do you like it when I finger your pussy?” 

Sam shivers again, this time for a completely different reason. The words wash over him in waves and Liam knows he got it right again when Sam lets out a moan and starts rocking on his finger. The lube warms as Liam works a second finger into Sam, as he draws another moan out of Sam. He works slowly, opening Sam up drawing out moans while he slowly praises him, his beautiful wife, his glorious and gorgeous woman. 

They do flip eventually, Liam more so feeling than watching as Sam sinks down on his cock, the red dress puffed out around him, his make-up smudged, and his hair sticking to his face. Once Sam bottoms out, they both take a moment to take a deep breath, the feeling of having Sam on his lap powerful, and especially with him dressed like this, it’s breathtaking. After a second Sam puffs out the hem of the dress, and it’s an image that Liam doesn’t think he’ll be able to get out of his head. He reaches up, and pushes the hair out of Sam’s face before trailing his fingers along his face, and eventually reaching to fondle his chest again. 

Sam starts moving it and it makes the picture even better. The curls in his hair slowly bouncing up and down as he moves, and his eyes half-closed in pleasure. Liam’s hips meet his movements, and as the younger man’s hand rest on his chest for leverage. Liam is pretty sure that this isn’t gonna last as long as Sam is hoping so after only a minute or so, Liam reaches for the back of the dress. 

He struggles for a second, mind hazy with Sam and everything that Sam is doing to and for him, and wanting more. He finally pops the top button of the dress and tries to fiddle with the ribbon holding the dress in place. Threw the whole process, Sam is incredible unhelpful continuing to rock on his cock, and laughing in Liam’s ear as he curses the complicated way that this dress is on. 

Eventually, the dress gets pulled over Sam’s head, and Liam is met with the sight of a bra holding Sam’s “breasts” in place. There is some type of padding in the bra, but that doesn’t matter to Liam right now, because right now his brain is nothing. He’s just slightly slack-jawed at the sight. A red bra with black lace that matches the panties that are discarded on the floor somewhere with the dress and Liam’s suit. Sam’s wig is somehow still in place, though much messer than it was before. Liam cards his fingers into his hair and pulls Sam down into a kiss. 

“I love you Sammy,” is all he whispers into the kiss, as their hips starting to find a pattern again. Liam can feel Sam smiling into the kiss, as one of Liam’s hands starts fondling Sam’s chest again, and the other wraps around Sam’s cock. 

It ends quickly after that. Between the lazy jerking of Sam’s cock, the fondling of his chest, Liam’s cock buried deep in him, and Liam’s tongue pushing into his mouth, Sam cums across Liam’s chest with a shout. And with a quick few more thrusts of his hips, Liam tumbles over the edge after him cumming deep in Sam. 

Sam crashes down onto Liam’s chest as he slowly pulls his softening dick out of him, the stickiness pressed between and the need to clean up pushed aside just for a moment to enjoy this moment of bliss

“Was I a good wife for you, Liam?” It’s Sam’s voice, not the higher-pitched voice he had been using all night. Liam pushes the hair from the wig off of his forehead, before pressing a kiss to it.  
“You were perfect, Sam, absolutely perfect,”

**Author's Note:**

> Dress Ref: https://solodress.storenvy.com/products/17684573-cute-red-knee-length-red-short-lace-christmas-party-dresses
> 
> Shoe Ref:https://www.lulus.com/products/dorian-dark-red-suede-lace-up-platform-heels/397662.html


End file.
